FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA

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Our top choices for Sheffield hotels

1. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (56 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is Rp3.114.672
Rp3.479.098 total
includes taxes & fees
7 Jul - 8 Jul
Wilder House Berkshires

2. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is Rp2.570.726
Rp2.871.502 total
includes taxes & fees
7 Jul - 8 Jul
The Yankee Inn

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (999 reviews)
"The staff was very helpful. It was very clean and the bed was comfortable. We would stay there again."
United States
Andrew
The price is Rp2.519.447
Rp3.215.271 total
includes taxes & fees
26 Jul - 27 Jul
Berkshire Mountain Lodge

4. the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (230 reviews)
"It’s a wonderful place to rest for a while. it has all you need, everything it’s in good conditions also it’s near of many activities like hiking."
United States
Daniel
The price is Rp3.051.840
Rp3.418.059 total
includes taxes & fees
1 Jul - 2 Jul
the Alander

5. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (778 reviews)
"very responsive staff excellent check in and check out"
United States
Kathleen
The price is Rp2.674.848
Rp2.987.751 total
includes taxes & fees
5 Jul - 6 Jul
Holiday Inn Express Hotel & Suites Great Barrington by IHG

6. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,000 reviews)
"Great staff breakfast was good location was close enough to walk but far enough from the noise "
United States
Braynd
The price is Rp2.370.562
Rp2.647.920 total
includes taxes & fees
29 Jun - 30 Jun
Quality Inn Great Barrington

7. Chatham Travel Lodge

Chatham Travel Lodge
2.5 star property
Old Chatham
7.8 out of 10, Good, (227 reviews)
"Very clean. Updated "
United States
jennifer
The price is Rp2.007.931
Rp2.248.668 total
includes taxes & fees
29 Jun - 30 Jun
Chatham Travel Lodge

8. Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (472 reviews)
"The parking is right in front of the cabin the breakfast is made to order, very nice place "
United States
William
The price is Rp1.211.580
Rp1.356.992 total
includes taxes & fees
29 Jun - 30 Jun
Berkshire Travel Lodge

9. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (424 reviews)
"Below average B&B"
United States
Larry
The price is Rp1.875.195
Rp2.156.474 total
includes taxes & fees
7 Jul - 8 Jul
Locust Tree Bed and Breakfast LLC

10. Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very good, (303 reviews)
"Great staff and location!"
United States
Stacie
The price is Rp4.023.043
Rp4.626.499 total
includes taxes & fees
1 Jul - 2 Jul
Interlaken Inn & Resort

11. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (874 reviews)
"I was pleasantly surprised how clean,spacious,quiet and comfortable the room was ( two queens) Loved the place."
United States
Yekaterina
The price is Rp1.995.365
Rp2.228.920 total
includes taxes & fees
30 Jun - 1 Jul
Monument Mountain Motel

12. The Brooks Motel

The Brooks Motel
2.0 star property
Hillsdale
7.4 out of 10, Good, (139 reviews)
"Nice "
United States
Daljit
The price is Rp2.504.304
Rp2.804.820 total
includes taxes & fees
28 Jun - 29 Jun
The Brooks Motel

13. The Whitlock

The Whitlock
2.0 star property
Lenox
8.6 out of 10, Excellent, (312 reviews)
"A beautiful old inn in the heart of a lovely old town."
United States
Linda
The price is Rp2.782.201
Rp3.107.718 total
includes taxes & fees
6 Jul - 7 Jul
The Whitlock

14. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (587 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
United States
Heather
The price is Rp1.597.728
Rp1.784.663 total
includes taxes & fees
29 Jun - 30 Jun
Travelodge by Wyndham Great Barrington Berkshires

15. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (788 reviews)
"Dawn was super helpful in getting us checked in."
United States
Kristen
The price is Rp3.646.949
Rp4.073.642 total
includes taxes & fees
19 Jul - 20 Jul
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

16. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,000 reviews)
"It was a clean, friendly hotel."
United States
Cheri
The price is Rp2.711.650
Rp3.028.861 total
includes taxes & fees
7 Jul - 8 Jul
Quality Inn Lee - Lenox South

17. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (189 reviews)
"beautiful inn"
United States
Maura
The price is Rp2.780.646
Rp3.197.742 total
includes taxes & fees
8 Jul - 9 Jul
Blackberry River Inn

18. Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (88 reviews)
"Excellent lodge, recommend."
United States
Jason
The price is Rp3.958.416
Rp4.433.427 total
includes taxes & fees
9 Jul - 10 Jul
Little Cat Lodge

19. Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (165 reviews)
"A charming stopover on our weekend travels. Small, quiet and lovely. Nice conversation with the host over breakfast too."
United States
Janice
The price is Rp3.881.654
Rp4.463.857 total
includes taxes & fees
6 Jul - 7 Jul
Cornwall Inn and Lodge

20. Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.6 out of 10, (91 reviews)
"A little dated but clean. A room for the night for when I race at lime rock"
United States
William
The price is Rp2.321.670
Rp2.669.921 total
includes taxes & fees
3 Jul - 4 Jul
Hitching Post Country Motel
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Stay near popular Sheffield attractions

Learn more about Sheffield

Tucked in the Berkshires, this charming town offers scenic hikes at Bartholomew's Cobble and local art at the Sheffield Historical Society. Catch live performances at the Berkshire Theatre Festival in nearby Stockbridge or sample farm-fresh produce at the weekend farmers' market on the town green.

FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA

Top Sheffield Hotel Reviews

More cheap stays in Sheffield

Find out more about Sheffield

Top reasons to visit Sheffield

  • Outdoor Adventures: Sheffield is a haven for outdoor enthusiasts, offering skiing, hiking, and exploring picturesque lakes and nature reserves.
  • Family-Friendly Activities: Enjoy apple picking and exciting rides, making it ideal for memorable family outings.
  • Art and Culture: Discover a variety of art galleries that showcase local talent and creativity.
  • Charming Atmosphere: Experience the warmth of friendly locals and a welcoming community in the beautiful Berkshires.
  • Diverse Accommodation: From agritourism to cosy bed and breakfasts, Sheffield has unique stays catering to every traveller.

Find great hotels near Sheffield

Experience the charm of Sheffield, Massachusetts, with a variety of accommodation options that cater to every traveller's needs. From delightful agritourism properties to inviting bed and breakfasts, Sheffield offers pet-friendly and family-oriented stays perfect for your adventure. Explore nearby attractions while enjoying a comfortable retreat in this picturesque town, with additional options available in Great Barrington for an unforgettable holiday experience.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: This charming 3.5-star resort offers a delightful blend of leisure and adventure, making it an ideal choice for families and business travellers alike. Nestled 19.3km from Sheffield, the resort features a variety of amenities, including an onsite mini-golf course, an arcade game room, and a playground to keep children entertained. The proximity to ski shuttles and lifts ensures that winter sports enthusiasts can easily access the slopes. With spacious accommodations and family-friendly services, this resort is perfect for a memorable vacation in the Berkshires.
  • Quality Inn: Located 9.7km from Sheffield, Quality Inn is the perfect base for adventure seekers and business travellers. Guests can enjoy a range of outdoor activities, from downhill skiing to hiking and biking, all available in the surrounding areas. The hotel’s focus on adventure sports makes it an exciting option for those looking to explore the natural beauty of the region. With comfortable lodging and easy access to recreational facilities, Quality Inn caters to those with an adventurous spirit while providing essential amenities for a productive stay.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Situated 11.3km from Sheffield, this hotel welcomes travellers with its inclusive atmosphere and modern comforts. Known for being LGBTQIA-friendly, it provides a warm environment for all guests. The property is well-equipped for business travel, featuring meeting spaces and complimentary Wi-Fi. Guests appreciate the contemporary design and convenient location, which offers easy access to local attractions. With attentive service and a focus on providing a comfortable experience, this hotel is an excellent choice for both leisure and business stays.

Where to stay near Sheffield

Sheffield, Massachusetts, offers an enchanting blend of adventure and history, perfect for an outdoor getaway. Nestled in the beautiful Berkshires, visitors can revel in stunning scenery, charming evenings, and a family-friendly atmosphere. Nearby attractions provide a romantic vibe, with friendly locals enhancing the experience. Whether you seek thrilling activities or a relaxing retreat, Sheffield and its surroundings promise a memorable stay, complemented by some of the best hotels in the region.

  • The Berkshires: Nestled 17.7km from Sheffield, The Berkshires is a stunning region renowned for its breathtaking outdoor experiences, making it a perfect destination for adventure seekers. With a blend of scenic mountains and serene lakes, this area is ideal for skiing in the winter and hiking in the summer. The Berkshires is not only about natural beauty—it's also home to various cultural events and venues, including conferences and festivals, which attract visitors year-round, particularly in the warmer months from June to August.
  • Great Barrington: Located 9.7km from Sheffield, Great Barrington is a vibrant city that draws visitors with its dynamic outdoor lifestyle and sporting opportunities. Known for its excellent skiing facilities, this area is a favourite among winter sports enthusiasts. During your visit, explore the local parks and lakes that offer tranquil spots for relaxation and picnicking. Great Barrington sees a peak in visitors from June to August, making it an exciting summer destination that balances adventure with community events.
  • South Egremont: Just 8.0km from Sheffield, South Egremont is a charming city that invites adventure lovers to experience its ski resorts and recreational activities. This area, like its neighbours, boasts stunning landscapes featuring mountains and lakes, perfect for both winter sports and summer excursions. South Egremont attracts a steady stream of visitors throughout the year, with a notable influx during the summer months. The nearby national state park offers additional opportunities for exploration and immersion in nature.

Things to do near Sheffield

Sheffield, Massachusetts, offers a delightful mix of outdoor adventures and family-friendly activities. Visitors can enjoy skiing at local resorts, partake in apple picking, and explore various art galleries. The area is perfect for day trips and exciting rides, making it an ideal destination for memorable family outings amidst the beautiful New England scenery.

Shopping

In Sheffield, you can enjoy shopping at local gems like Hoffman's Pottery for unique items. If you're up for a drive, Lee Premium Outlets, located 22.5km away, offers a variety of brand-name stores, while the Berkshire Mountain Country Store, 24.1km away, features charming local goods.

Recreation

Lake Mansfield Park, a tranquil retreat 11.3km from Sheffield, offers serene walking trails and picturesque views, perfect for relaxation. Music Mountain, located 20.9km away, hosts vibrant concerts, while Undermountain Golf Course, 14.5km from town, provides an invigorating outdoor experience for golf enthusiasts.

Adventure

At Ski Butternut, 8.0km from Sheffield, experience exhilarating skiing amidst a vibrant sports atmosphere. The Housatonic River Walk, located 9.7km away, offers breathtaking scenery for hikers seeking outdoor adventure. For thrill-seekers, Catamount Aerial Adventure Park, 12.9km from Sheffield, features an exciting zipline and ropes course.

Nightlife

In Sheffield, the Mahaiwe Performing Arts Center offers a charming atmosphere with captivating performances just 9.7km away. Infinity Music Hall and Bistro, located 17.7km away, blends exquisite dining with live entertainment. For a rich cultural experience, the Berkshire Theatre Festival is only 19.3km from Sheffield.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Sheffield

To save money on your trip to Sheffield, consider visiting during the off-peak months of January and March to April, when accommodation prices are lower. Booking your stay for a Tuesday can also help you find cheaper rates, while Saturdays tend to be the most expensive. Use Expedia’s search tool to filter by budget, location, and hotel type, including eco-certified options. You can further save by bundling your hotel, flights, and activities into a package deal, ensuring you get the best value for your stay.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Sheffield are January and March to April, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Sheffield is Tuesday. The most expensive day to stay in Sheffield is Saturday.
  • Find cheap hotels on Expedia: Expedia’s search tool enables you to set your budget, choose your ideal location, and much more. You can arrange your search results to display prices from lowest to highest, allowing you to find the most affordable hotels first. Additionally, you can refine your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels available for booking.
  • Consider bundling your trip: You can save money by combining your hotel reservation in Sheffield with your flights and activities through an Expedia package.

Find the best attractions near Sheffield

Sheffield, Massachusetts, is an excellent destination for adventure seekers and outdoor enthusiasts, offering a variety of activities such as skiing and exploring nature. Visitors can enjoy nearby national parks, nature reserves, and picturesque lakes, making it ideal for eco-friendly experiences. Whether you’re hiking, skiing, or simply soaking in the natural beauty, Sheffield promises an unforgettable outdoor vacation.

  • Bash Bish Falls State Park: Located 11.3km away from Sheffield, this stunning park features breathtaking waterfalls surrounded by lush greenery. It offers a perfect blend of adventure and tranquillity, with hiking trails that lead you through picturesque landscapes.
  • Housatonic River: Just 9.7km from Sheffield, the Housatonic River is a serene spot ideal for picnicking and scenic walks. Its beautiful banks provide a peaceful atmosphere where you can enjoy the natural beauty and perhaps spot some local wildlife.
  • Three Mile Pond Wildlife Management Area: Only 3.2km from Sheffield, this nature reserve is an eco-friendly haven. It's perfect for outdoor enthusiasts seeking adventure, with opportunities for birdwatching and exploring diverse habitats.

Best time to go to Sheffield

The best time to visit Sheffield is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January23.2°F (-4.9°C)Light RainMostly CloudyAverageSlightly Low
February24.8°F (-4.0°C)Light RainMostly CloudySlightly LowAverage
March32.5°F (0.3°C)Light RainMostly CloudyAverageSlightly Low
April44.2°F (6.8°C)Light RainMostly CloudyAverageSlightly Low
May55.9°F (13.3°C)Light RainMostly SunnyAverageAverage
June63.7°F (17.6°C)Light RainMostly SunnySlightly HighAverage
July69.8°F (21.0°C)Light RainMostly SunnySlightly HighSlightly High
August67.8°F (19.9°C)Light RainMostly SunnyAverageSlightly High
September60.8°F (16.0°C)Light RainMostly SunnySlightly HighAverage
October49.8°F (9.9°C)Light RainMostly SunnyAverageSlightly High
November37.8°F (3.2°C)Light RainMostly SunnySlightly LowAverage
December29.7°F (-1.3°C)Light RainMostly CloudySlightly LowAverage

The nearest major airports for your trip to Sheffield

To visit Sheffield, Massachusetts, you can fly into several major airports. Hartford, CT (BDL-Bradley Intl.) is 59.5km away, with nearby hotels such as the Sheraton Hartford Hotel at Bradley Airport and The Capitol Hotel, both offering convenient access via airport shuttles. Albany, NY (ALB-Albany Intl.) is 80.5km distant, featuring hotels like Oakcliff Bed and Breakfast and Four Points by Sheraton Albany, easily reachable from the airport. Finally, Newburgh, NY (SWF-Stewart Intl.) is 91.7km away, with options like The Crossroads Hotel and Comfort Suites Fishkill, both accessible via local transportation services. Each airport provides a variety of accommodation choices to enhance your stay.

Frequently asked questions

Where is the best place to stay in Sheffield?
Wilder House Berkshires is one of the top choices for your stay based on our traveller data. This B&B offers free breakfast and free parking. Two other options for your trip to the area are The Yankee Inn and Berkshire Mountain Lodge. See all available top hotels, or vacation rentals in Sheffield.
If I need to cancel my hotel reservation in Sheffield, will I receive a refund?
Yes, the majority of hotel reservations are fully refundable provided that you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If your reservation is non-refundable, it may still be possible to cancel it and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Sheffield.
What are some accommodation options with pools in Sheffield?
The Yankee Inn: Offers a seasonal outdoor pool, an indoor pool and buffet. Berkshire Mountain Lodge and The Red Lion Inn are a couple of other choices that feature an on-site pool. View all hotels with pools in Sheffield.
What's it like staying in Sheffield?
Visitors can enjoy all that Sheffield has to offer, including the casinos and local tours. In Sheffield, there are 30 hotels and other accommodation options to choose from. Find out more about Sheffield.
What are the top places to visit in Sheffield?
The picturesque setting of Housatonic River and Bartholomews Cobble exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are Magnolia Bluffs Casino and Bartholomew's Cobble. Take a look at what more there is to see and do in Expedia's Sheffield guide.
What's the seasonal weather like in Sheffield?
The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Sheffield are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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